Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes

Fu-Min Liao; Zhong-Yan Cao; Jin-Sheng Yu; Jian Zhou

doi:10.1002/anie.201611625

Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes

Angew Chem Int Ed Engl. 2017 Feb 20;56(9):2459-2463. doi: 10.1002/anie.201611625. Epub 2017 Jan 18.

Authors

Fu-Min Liao¹, Zhong-Yan Cao¹, Jin-Sheng Yu¹, Jian Zhou^{1

2}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, 3663N Zhongshan Road, Shanghai, 200062, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 200032, China.

PMID: 28097773
DOI: 10.1002/anie.201611625

Abstract

We report a highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C-F bond as a synthetic handle. Cationic Au^I catalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.

Keywords: coupling reactions; diazo reagents; fluorine effects; gold catalysis; olefination.

Publication types

Research Support, Non-U.S. Gov't